Sodium → HCID 54169835, compound

HRID 2417861Notes

Reaction equation

HRID 2417861 reaction equation
C([O:4][C@@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43]C(=O)C)[C@@H:35]([O:36]C(=O)C)[C@H:30]([O:31]C(=O)C)[C@H:25]2[O:26]C(=O)C)[C@@H:16]([CH2:47][O:48]C(=O)C)[O:15][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([SH:14])[CH:9]=1)(=O)C.[Na]>CO>[C@H:24]1([O:23][C@@H:17]2[C@@H:16]([CH2:47][OH:48])[O:15][C@@H:6]([S:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([SH:14])[CH:9]=3)[C@H:5]([OH:4])[C@H:18]2[OH:19])[O:41][C@H:40]([CH2:42][OH:43])[C@@H:35]([OH:36])[C@H:30]([OH:31])[C@H:25]1[OH:26]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 13384945HCID 13384945, compound

Product 1

HCID 54169835HCID 54169835, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.1 g of 3-mercaptophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 50 ml of methanol was added 0.15 g of sodium spheres. The reaction was stirred 3 hours, concentrated in vacuo and warmed with 50 ml of methanol:water (1:1). This reaction was filtered, the filtrate stirred with Dowex® 50WX8 resin and refiltered. This filtrate was concentrated in vacuo, giving 2.7 g of the desired intermediate as a yellow solid, [α]D26 =+81°±1° (0.818%, methanol).

Workup

  1. concentrationconcentrated in vacuo
  2. temperaturewarmed with 50 ml of methanol:water (1:1)
  3. filtrationThis reaction was filtered
  4. stirringthe filtrate stirred with Dowex® 50WX8 resin
  5. concentrationThis filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a4ffce06fd42490c9c037f618a0b8d1a
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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